Skip to main content
SpringerLink
Log in

Synthesis and Fungicidal Activity of 4-[(Alkylsulfanyl)methyl]-3,5-dimethylisoxazoles

  • Organic Synthesis and Industrial Organic Chemistry
  • Published:
Russian Journal of Applied Chemistry Aims and scope Submit manuscript

Abstract

Previously unknown 4-[(alkylsulfanyl)methyl]-3,4-dimethylisoxazoles were prepared by the reaction of accessible 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with hydroxylamine in ethanol under microwave irradiation and without it. Performing the heterocyclization under the conditions of microwave irradiation allows the reaction time to be decreased to 15 min and the yields to be increased to 89–95%. 4-[(Butylsulfanyl)methyl]-3,5-dimethylisoxazole exhibits antifungal activity toward Rhizoctonia solani and Fusarium oxysporum phytopathogenic fungi.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Lamberth, C., J. Heterocycl. Chem., 2017, vol. 55, no. 9, pp. 2035–2045. https://doi.org/10.1002/jhet.3252

    Article  CAS  Google Scholar 

  2. Agrawal, N. and Mishra, P., Med. Chem. Res., 2018, vol. 27, no. 5, pp. 1309–1344. https://doi.org/10.1007/s00044-018-2152-6

    Article  CAS  Google Scholar 

  3. Lin, X., Li, Y., Zhong, W., Hong, T., Li, L., Song, S., and He, D., J. Agric. Food Chem., 2021, vol. 69, no. 33, pp. 9520−9528. https://doi.org/10.1021/acs.jafc.1c01816

    Article  CAS  Google Scholar 

  4. Chen, F., Han, P., Liu, P., Si, N., Liu, J., and Liu, X., Sci. Rep., 2014, vol. 4, ID 6473. https://doi.org/10.1038/srep06473

    Article  CAS  Google Scholar 

  5. Sun, J. and Zhou, Y., Molecules, 2015, vol. 20, no. 3, pp. 4383–4394. https://doi.org/10.3390/molecules20034383

    Article  CAS  Google Scholar 

  6. Morita, T., Yugandar, S., Fuse, S., and Nakamura, H., Tetrahedron Lett., 2018, vol. 59, no. 13, pp. 1159–1171. https://doi.org/10.1016/j.tetlet.2018.02.020

    Article  CAS  Google Scholar 

  7. Vasilenko, D.A., Dronov, S.E., Parfiryeu, D.U., Sadovnikov, K.S., Sedenkova, K.N., Grishin, Y.K., Rybakov, V.B., Kuznetsova, T.S., and Averina, E.B., Org. Biomol. Chem., 2021, vol. 19, pp. 6447–6454. https://doi.org/10.1039/d1ob00816a

    Article  CAS  Google Scholar 

  8. Gao, W., Cheng, Y., Chang, H., Li, X., Wei, W., and Yang, P., J. Org. Chem., 2019, vol. 84, no. 7, pp. 4312–4317. https://doi.org/10.1021/acs.joc.9b00256

    Article  CAS  Google Scholar 

  9. Padmaja, A., Payani, T., Dinneswara Reddy, G., and Padmavathi, V., Eur. J. Med. Chem., 2009, vol. 44, no. 11, pp. 4557–4566. https://doi.org/10.1016/j.ejmech.2009.06.024

    Article  CAS  Google Scholar 

  10. Lavanya, G., Reddy, L.M., Padmavathi, V., and Padmaja, A., Eur. J. Med. Chem., 2014, vol. 73, pp. 187–194. https://doi.org/10.1016/j.ejmech.2013.11.041

    Article  CAS  Google Scholar 

  11. Laboratorni Technica Organicke Chemie, Keil, B., Ed., Prague: Ceskoslov. Akad. Ved, 1963.

    Google Scholar 

  12. Baeva, L.A., Biktasheva, L.F., Fatykhov, A.A., and Lyapina, N.K., Russ. J. Org. Chem., 2013, vol. 49, no. 9, pp. 1283–1286. https://doi.org/10.1134/S1070428013090078 

    Article  CAS  Google Scholar 

  13. Baeva, L.A., Nugumanov, R.M., Fatykhov, A.A., and Lyapina, N.K., Russ. J. Org. Chem., 2018, vol. 54, no. 3, pp. 444–451. https://doi.org/10.1134/S1070428018030120 

    Article  CAS  Google Scholar 

  14. Bonev, B., Hooper, J., and Parisot, J., J. Antimicrob. Chemother., 2008, vol. 61, no. 6, pp. 1295–1301. https://doi.org/10.1093/jac/dkn090

    Article  CAS  Google Scholar 

  15. Jin, R.Y., Sun, X.H., Liu, Y.F., Long, W., Chen, B., Shen, S.Q., and Ma, H.X., Spectrochim. Acta, Part A: Mol. Biomol. Spectrosc., 2016, vol. 152, pp. 226–232. https://doi.org/10.1016/j.saa.2015.07.057

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

IR and 13С, 1Н NMR studies, analysis by liquid chromatography–mass spectrometry, and elemental analysis were performed using the equipment of the Chemistry Center for Shared Use, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The study was performed within the framework of government assignments (theme nos. 122031400274-4 and 122031100163-4).

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Bashkortostan, Russia

    L. A. Baeva, L. F. Biktasheva & A. A. Fatykhov

  2. Ufa Institute of Biology, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Bashkortostan, Russia

    N. F. Galimzyanova

Authors
  1. L. A. Baeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. F. Biktasheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Fatykhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. F. Galimzyanova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to L. A. Baeva or N. F. Galimzyanova.

Ethics declarations

The authors declare that they have no conflict of interest.

Additional information

Translated from Zhurnal Prikladnoi Khimii, No. 7, pp. 938–944, July, 2022 https://doi.org/10.31857/S0044461822070142

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baeva, L.A., Biktasheva, L.F., Fatykhov, A.A. et al. Synthesis and Fungicidal Activity of 4-[(Alkylsulfanyl)methyl]-3,5-dimethylisoxazoles. Russ J Appl Chem 95, 1030–1035 (2022). https://doi.org/10.1134/S1070427222070151

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070427222070151

Keywords:

Search

Navigation